Diosmin, 地奥斯明 

Anti-inflammatory, antioxidant and antitumor agent. Potentiates SOD, catalase and glutathione peroxidase activity. Anti-ischemic effects in vivo. Orally active.

Diosmin is a flavonoid that has been found in citrus fruits and has diverse biological activities. It inhibits LPS-induced production of prostaglandin E2 (PGE2;), nitric oxide (NO), IL-12, IL-6, and TNF-α in RAW 264.7 macrophages when used at concentrations ranging from 10 to 50 µM. Diosmin (100 mg/kg) reduces gastric ulcer area and leukocyte invasion in a rat model of ethanol-induced gastric injury. It decreases lung malondialdehyde (MDA) levels, increases lung glutathione (GSH) levels and catalase activity, and reduces fibrosis in a mouse model of paraquat-induced lung injury. Diosmin (50 and 100 mg/kg) increases the time spent in the goal quarter in a spatial memory test and reverses hippocampal dentate gyrus long term potentiation impairments in a rat model of scopolamine-induced cognitive impairment. It also reduces mechanical and thermal hyperalgesia in a rat model of neuropathic pain induced by chronic constriction injury.

Diosmin analytical standard provided with w/w absolute assay, to be used for quantitative titration.

Diosmin is a disaccharide derivative that consists of diosmetin substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage. It has a role as an antioxidant and an anti-inflammatory agent. It is a glycosyloxyflavone, a rutinoside, a disaccharide derivative, a monomethoxyflavone and a dihydroxyflavanone. It derives from a diosmetin.

Diosmin is a semisynthetic drug indicated for the treatment of venous disease. Diosmin is a flavone that can be found in the plant Teucrium gnaphalodes. Diosmin is available as a prescription medicine in several European countries, and is available as a nutritional supplement in the United States and the rest of Europe. It should be noted that clinical studies have been inconclusive and no articles have been published pertaining to its use in the treatment of vascular disease. When used in rats, diosmin has been effective at mitigating hyperglycaemia, and may also have antineurodegenerative properties.

A bioflavonoid that strengthens vascular walls.

Phlebotropic drug used in the treatment of venous disease.

Title: Diosmin

CAS Registry Number: 520-27-4

CAS Name: 7-[[6-O-(6-Deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl]oxy]-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one

Additional Names: 3',5,7-trihydroxy-4'-methoxyflavone-7-rutinoside; 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-(O6-a-L-rhamnopyranosyl-b-D-glucopyranosyloxy)chromen-4-one; 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-b-rutinosyloxy-4H-chromen-4-one; diosmetin 7-b-rutinoside; barosmin; buchu resin

Trademarks: Diosmil (Bellon); Diosven (CT); Diovenor (Innothža); Flebosmil (Bouchara); Flebosten (Bonomelli); Hemerven (Interdelta); Insuven (Berenguer); Litosmil (Evans); Tovene (Kali-Chemie); Varinon (Exa); Ven-Detrex (Zyma); Venosmine (Geymonat)

Molecular Formula: C28H32O15

Molecular Weight: 608.54

Percent Composition: C 55.26%, H 5.30%, O 39.44%

Literature References: Naturally occurring flavonic glycoside; rhamnoglycoside of diosmetin, q.v. Isolation from various plant sources: O. A. Oesterle, G. Wander, Helv. Chim. Acta 8, 519 (1925). Elucidation of structure: G. Zemplén, R. Bognár, Ber. 76, 452 (1943). Prepn from hesperidin, q.v.: eidem, ibid.; N. B. Lorette et al., J. Org. Chem. 16, 930 (1951). Isoln from lemon peel (Citrus limon Linn. Rutaceae): R. M. Horowitz, J. Org. Chem. 21, 1184 (1956); from Zanthoxylum avicennae, Rutaceae: H. R. Arthur et al., J. Chem. Soc. 1956, 632; H. R. Arthur et al., ibid. 1959, 4007; from flowers of Sophora microphylla Ait. Leguminosae: L. H. Briggs et al., ibid. 1960, 1955. Toxicology studies: H. Heusser, W. Osswald, Arch. Farmacol. Toxicol. 3, 33 (1977). NMR spectrum: J. L. Nieto, A. M. Gutierrez, Spectrosc. Lett. 19, 427 (1986). Mechanism of action: C. Boudet, L. Peyrin, Arch. Int. Pharmacodyn. 283, 312 (1986). Pharmacology: J. R. Caseley-Smith, J. R. Caseley-Smith, Agents Actions 17, 1 (1985); M. Damon et al., Arzneim.-Forsch. 37, 1149 (1987). HPLC determn in biological fluids: D. Baylocq et al., Ann. Pharm. Fr. 41, 115 (1983). Clinical study in post-phlebitic ulcers: M. C. Nguyen, K. Morere, Gaz. Med. 92, 71 (1985); in acute hemorrhoids: A. Tajana et al., Minerva Med. 79, 387 (1988). Clinical trial in chronic venous insufficiency: R. Laurent et al., Int. Angiol. 7, Suppl. 2, 39 (1988).

Derivative Type: Monohydrate

Molecular Formula: C28H32O15.H2O

Molecular Weight: 626.56

Percent Composition: C 53.67%, H 5.47%, O 40.86%

Properties: mp 275-277° (dec) (Zemplén). Also reported as fine needles from aq pyridine or aq DMF, mp 283° (dec) (Briggs). uv max (ethanol): 255, 268, 345 nm (log e 4.28, 4.25, 4.30). Practically insol in water, alcohol.

Melting point: mp 275-277° (dec) (Zemplén); mp 283° (dec) (Briggs)

Absorption maximum: uv max (ethanol): 255, 268, 345 nm (log e 4.28, 4.25, 4.30)

Derivative Type: Flavonoid extract

Trademarks: Daflon (Servier); Flebopex (Profarma); Flebotropin (Bago)

Therap-Cat: Capillary protectant.

Keywords: Vasoprotectant.